Condensation product of a monoalkanolamine with the reaction product of a terpene and an alpha, beta-unsaturated polycarboxylic acid, anhydride, or ester thereof



, ment, discoloration, etc. objectionable because thesediment tends toplug burner This application is a continuation-in-part of my copendingapplication Serial No. 591,296, now Patent No.

2,974,024, March 7, 1961, filed June 14, 1956, and

relates to novel compositions of matter which are particularly useful asadditives for the stabilization of organic compounds and, moreparticularly, for use in preventing deterioration of said organiccompounds in storage, during transportation or in use. I

The novel additives of the present invention are particularlyadvantageous for use in the stabiliiation of a hydrocarbon distillateand serves to improve the hydrocarbon distillate in a number ofdifferent ways. For example, in fuel oils, burner oils, range oils,diesel oils,

' marine oils, turbine oils, cutting oils, rolling oils, soluble oils,drawing oils, slushing oils, slushing greases, lubricating oils,lubricating greases, fingerprint removers, etc., the distillate orgrease is improved in one or more ways including retarding and/ orpreventing sediment formation, dispersion of sediment when formed,preventing and/or retarding discoloration, oxidation inhibitor, rust orcorrosion inhibitor, detergent, etc. In lubricating type oils, inaddition to'all or some of the properties hereinbefore set forth, theadditive may function as a pour po ntdepressant, viscosity indeximprover, anti-foaming agent, extreme pressure additive, etc., Inliquefied petroleum gases, gasoline, naphtha, aromatic solvents,kerosene, jet fuels, etc., the additive serves as a corrosion inhibitoralong with one or more of the other functions mentioned above. In otherorganic compounds, including alcohols, ethers, aldehydes, ketones,chlorinated hydrocarbons, etc., and compositions containing them,glyceridio oils and fats, waxes, other oils and fats of animal orvegetable origin, rubber, resins, plastics, etc., the additive functionsas a beneficient in one or more of the manners herein set forth orotherwise.

The invention is particularly applicable to the stabilization ofhydrocarbon distillates heavier than gasoline. The hydrocarbondistillate may be cracked, straight ,run or 'mixtures thereof. Many fueloils and particularly blends of straight run and cracked fuel oilsundergo deterioration in storage, resulting in the formation of sedi-The formation of sediment is tips, injectors, etc. In diesel fuel, thedeterioration tends to form varnishand sludge in the diesel engine.Discoloration of fuel oils is objectionable for various easons,including customerspreference forlight colored oils.

In handling of hydrocarbon distillates and othero'rganic liquids, it isoftennecessary to transport and/or-store such materials in metalcontainers, as in steel or other metal pipe lines, drums, tanks, etc.Since these materials often contain varying amounts of water in solutionor insuspension which may separate, due totemperature changes, internalcorrosion of the container by separating water almost invariably occursto a greater or lesser degree. The water thus separated forms as a filmor in minute droplets in the pipe line or on the container walls or evenin small pools at the bottom of the container. This brings about idealconditions for corrosion and consequent damage to the metal surfaces ofthe container, as well S a e Pat as the serious contamination of thehydrocarbon oil or other materials contained therein by the corrosionproducts.

Corrosion problems also occur, for example, in the lubrication ofinternal combustion engines or steam engines, including turbines andother similar machinery, in which a quantity of water is often observedas a separate phase within the lubricating system as a result of thecondensation of water from the atmosphere or, in the case of internalcombustion engines, as the result of dispersion or absorption inlubricating oil of Water formed as a product of fuel combustion. Waterin such instances corrodes the various metal parts of the machinery withwhich it comes into contact, the corrosion products causing furthermechanical damage to bearing surfaces and the like due to their abrasivenature and catalytically promoting the chemical degradation of thelubricant. Corrosion problems also arise in the preparation,transportation and use of various coating compositions such as greases,household oils, paints, lacquer, etc., which often are applied to metalsurfaces for protective purposes.

In one embodiment the present invention relates to a novel compositionof matter comprising the condensation product of an alkanolamine withthe reaction product of a terpene and a compound selected from the groupconanhydride or ester formed by the reaction of a terpenic compound withan alpha,beta-unsaturated polycarboxylic acid, anhydride or esterthereof.

Any suitable alkanolamine, and particularly a monoalkanolarnine, is usedin accordance with the present invention. Preferably the alkanolamine isan N-hydrocarbon substituted alkanolamine, the hydrocarbon substituentpreferably comprising an aliphatic group containing from about 6 toabout 50 carbon atoms'per molecule, although it may comprise an aryl orcycloalkyl group. It is particularly preferred that the N-alkylalkanolamine contains from about 15 to about 40 carbon atoms in thealkyl substituent and that the nitrogen atom and hydroxyl group areseparated by not more than four carbon atoms.

A particularly preferred N-substituted alkanolamine comprises an N-alkylethanolamine. Illustrative compounds include N-hexyl ethanolamine,N-heptyl ethanoL amine, N-octyl ethanolamine, N-nonyl ethanolamine,N-decyl ethanolamine, N-undecyl ethanolamine, N-dodecyl ethanolamine,N-tridecyl ethanolamine, N-tetradecyl ethanolamine, N-pentadecylethanolamine, N-hexaamine, N-pentatetracontyl ethanolamine,N-hexatetracontyl ethanolamine, N-heptatetracontyl ethanolamine,N-octatetracon-tyl ethanolamine, N-nonatetracontyl ethanolamine,N-pentacontyl ethanolamine, etc. In some cases, N-al kenyl ethanolaminesmay be utilized. Illustrative N-alkenyl ethanolamines include N-hexenylethanolamine, N-heptenyl ethanolamine, N-octenyl ethanolamine, N-nonenylethanolarnine, N-decenyl ethanolamine, N-undecenyl ethanolamine,N-dodecenyl cthanolamine, N tridecenyl ethanolamine, N-tetradecenylethanolamine, N-pentadecenyl ethanolamine, N-hexadecenyl ethanolamine,N-heptadecenyl ethanolamine, N-octa decenyl ethanolamine, N-nonadecenylethanolamine, N-eicosenyl ethanolamine, etc.

It is understood that the -N-aliphatic ethanolamines may containaliphatic substituents attached to one or both of the carbon atomsforming the ethanol group. These compounds may be illustrated byN-aliphatic-Z-hydroxypropylamine, N-aliphatic 2 hydroxy-butylamine,N-aliphatic 2 hydroxy-amylamine, N-aliphatic 2 hydroxyhexylamine,N-aliphatic 2 hydroxy-heptylamine, N-aliphatic-Z-hydroxy-octylamine,etc., 2-(N-aliphatic-amino)- propanol, Z-(N-aliphaticamino)-butanol,Z-(N-aliphaticamino)-pentanol, Z-(N-aliphaticamino)-hexanol, 2-(N-aliphatic-amino) -heptanol, 2- (N-aliphaticamino) -octanol, etc.,Z-(N-aIiphatieamino) 1 methylpropanol, Z-(N-aliphaticamino-1-methylbutanol, 2- (N-aliphaticamino) -1- methylhexanol,2-(N-aliphaticamino)-1-methylhep=tanol,2(N-aliphaticamino)-1-methyloctanol, etc. It will be noted that,although named as an amine or alkanol, these compounds are ethanolaminesas they contain the ethanol and amine groupings. It is understood thatthese specific compounds are illustrative only and that other suitablecompounds containing the ethanolamine configuration may be employed.

The specific compounds hereinbefore set forth are examples ofN-aliphatic-ethanolamines. Other preferred N-aliphatic alkanolaminesinclude N-aliphatic-propanolamines and N-aliphatic-butanol-amines,although N-aliphatic-pentanolamines, N-aliphatic-hexanolamines andhigher al-kanolamines may be used in some cases. It is understood thatthese alkanolamines may be substituted in a manner similar to thatspecifically described hereinbefore in connection with the discussion ofthe ethanolamines. Furthermore, it is understood that mixtures ofN-aliphatic-alkanolamines may be employed, these preferably beingselected from those hereinbefore set forth. Also, it is understood thatmixtures of the monoalkanolamine with polyalkanolamines and particularlyN-substituted polyalkanolamines may be employed. Likewise, it isunderstood that the various alkanolamines are not necessarilyequivalent.

As hereinbefore set forth, the N-aliphatic alkanolamine is reacted withan alpha,beta-unsaturated polycarboxylic acid, anhydride or ester formedby the reaction of a terpene with an alpha,beta-unsaturatedpolycarboxylic acid, anhydride or ester. The reaction product willcomprise primarily the anhydride but the acid and/or ester also will bepresent. Any suitable terpenic compound may be reacted with any suitablealphabeta-unsaturated polycarboxylic acid, anhydride or ester to formthe reaction product for subsequent condensation with the alkanolamine.In one embodiment a terpene hydrocarbon having the formula C H isemployed, including alphapinene, beta-pinene, dipentene, d-limonene,l-limonene and terpinoline. These terpene hydrocarbons have boilingpoints ranging from about 150 to about l85 C. In another embodiment theterpene may contain three double bonds in monomeric form, includingterpenes as allo-o-cymene, o-cymene, myrcene, etc. Other terpeniccompounds include alpha-terpinene, p-cyrnene, etc. Also included asterpenic compounds are rosins comprising the terpenic hydrocarbons and/or tenpenic acids. These rosins and acids generally are tricycliccompounds.

However, they are obtained from pine trees and therefore may be includedin the broad classification as terpene or terpenic compounds.

As hereinbefore set forth, the terpene is reacted with analpha,beta-unsaturated polycarboxylic acid, anhydride or ester thereof.Any unsaturated polycarboxylic acid having a point of unsaturationbetween the alpha and beta carbon atoms may be employed. Illustrativeunsaturated dicarboxylic acids include maleic acid, fumaric acid,citraconic acid, mesaconic acid, aconitic acid, itaconic acid. While thedicarboxylic acids are preferred, it is understood thatalpha,beta-unsaturated polycarboxylic acids containing three, four ormore carboxylic acid groups may be employed. Furthermore, it isunderstood that a mixture of alpha,beta-unsaturated polycarboxylic acidsand particularly of alpha,beta-unsaturated dicarboxylic acids may beused.

While the alpha,beta-unsaturated polycarboxylic acid may be employed,advantages appear to be obtained in some cases when using the anhydridesthereof. Illustrative anhydrides include maleic anhydride, citraconicanhydride, aconitic anhydride, itaconic anhydride, etc. It is understoodthat a mixture of anhydrides may be employed and also that the anhydridemay contain substituents and particularly hydrocarbon groups attachedthereto. Furthermore, itis understood that the various anhydrides arenot necessarily equivalent. Also, it is understood that esters of thealpha, beta-unsaturated polycarboxylic acids may be employed, the estergroup being selected from alkyl, alkaryl, aralkyl, aryl and cycloalkylsubstituents replacing one or more of the hydrogen atoms of thecarboxylic acid groups.

The reaction of terpene and alpha,beta-unsaturated polycarboxylic acid,anhydride or ester generally is effected at a temperature of from about150 to about 300 C., and preferably of from about 160 to about 200 C.The time of heating will depend upon the particular reactants and mayrange from 2 hours to 24 hours or more. When desired, a suitable solventmay be utilized. Following the reaction, impurities or unreactedmaterials may be removed by vacuum distillation or otherwise, to leave aresinous product which may be a viscous liquid or a solid.

A terpene-maleic anhydride reaction product is available commerciallyunder the trade name of Petrex Acid. This acid is a stringy,yellow-amber colored mass and is mostly dibasic. It has an acid numberof approximately 530, a molecular weight of approximately 215 and asoftening point of 4050 C.

Another reaction product is available commercially under the trade nameof Lewisol 40 Acid. This is a tricarboxylic acid and is formed by thereaction of fumaric acid and rosin. It is a hard, brittle solid having asoftening point of 150-160 C. and a specific gravity at 25/25 C. of1.178.

The condensation of the alkanolamine and reaction product of terpene andalpha,beta-unsaturated polycarboxylic acid, anhydride or ester may beeffected in any suitable manner. The reaction generally is effected at atemperature above about .80 C. and preferably at a higher temperaturewhich usually will not exceed about 200 C., although higher or lowertemperatures may be employed under certain conditions. The exacttemperature will depend upon whether a solvent is used and, whenemployed, on the particular solvent. For example, with benzene as thesolvent, the temperature will be in the order of C., with toluene thetemperature will be in the order of C., and with xylene in the order of155 C. Other preferred solvents include cumene, naphtha, decalin, etc.Any suitable amount of the solvent may be employed but preferably shouldnot comprise a large excess because this will tend to lower the reactiontemperature and slow the reaction. Water formed during the reaction maybe removed in any suitable manner including, for example, by operatingunder i any suitable manner.

reduced pressure, by removing an azeotrope of watersolvent, bydistilling the reaction product at an elevated temperature, etc. Ahigher temperature may be utilized in effecting the reaction in order.to remove the-water as it is being formed. However, for many uses, thereaction need not go to completion, but in any event at least asubstantial portion of the reaction product will comprise that formed bythe condensation of the alkanolamine with the terpene-acid, anhydride orester reaction product.

In general the condensation is effected using equivalent acid orpotential acid groups per total amino and hydroxyl groups. However, itis understood that the total acid or potential acid groups may rangefrom about 0.5 to about 2. equivalents thereof per equivalent of totalamino and hydroxyl groups.

From the above description, it will be noted that a number of differentcompounds may be prepared and used in accordance with the presentinvention, and will depend upon specific alkanolamine and terpene-acid,anhydride or ester reaction product used in thecondensation reaction.However, it is understood that, while all of these compounds will beeffective in certain substrates, all are not necessarily equivalent inthe same or different substrate. 1

The condensation product is recovered as a viscous liquid or solid. Insome cases, the product will .be marketed and utilized as a-solution ina solvent. Conveniently, this solvent comprises the same solvent used inpreparing the condensation product and is recovered in admixture with atleast a portion of the solvent, thereby avoiding the necessity ofremoving all of the solvent and subsequently adding it back. When a moredilute solution is desired than is recovered in the manner hereinbeforeset forth, it is understood that the same or different solvent may becommingled with the mixture to form a solution of the desiredconcentration.

aer te;

tains the sediment dispersed throughout the oil. As hereinbefore setforth, dispersing the sediment throughout the fuel oil allows thesediment to pass through filters, burner tips, etc., whereassedimentation will result in clogging of the fuel oil lines, filters,burner tips, etc.

1 In still another test, referred to as the Erdco Test,

, heated oil is passed through a filter and the time required Theconcentration; of additive to be usedin the organic substrate willdepend upon the particular substrate and the particular benefitsdesired.In general, the additive will be used in a concentration of from about0.0000l% to about 5% by weight or more and more specifically is used ina concentration of from about 0.0001% to about 1% by weight of thesubstrate. The additive may be used along with other additives which areincorporated in a substrate for specific purposes including, forexample, metal deactivators, antioxidants, antiozidants, synergists,dyes, fuel improvers, etc. i

The additive maybe incorporated in the substrate in As here-inbefore setforth, the additive conveniently is marketed as a solution in a suitablesolvent, including hydrocarbons and particularly aromatic hydrocarbonsas benzene, toluene, xylene, cumene, etc. 'When the additive is to beincorporated in a liquid substrate, it may be added thereto in thedesired amount and the resultant. mixture suitably agitated or otherwisemixed in order to obtain intimate admixing of the additive in thesubstrate. When the additive is to be utilized as a corrosion inhibitorin plant equipment, it may be introduced into a fractionator, vapor lineor at any other suitable point in, order to prevent corrosion of theplant equipment. In this embodiment, the additive carries over into theproduct of the process and, also serves thereinas a beneficent; It isunderstood that a' portion of the additive may be introduced into theplant equipment and an additional portion of the additive incorporatedin the effiuent product when so desired.

The following examples are introducedto illustrate further the noveltyand utility of the present invention but not with the intention ofunduly limiting the same.

A number of additives were prepared and were tested bytwo differentmethods. In one method, referred to as the Fuel Oil Suspension Test,powdered carbon black (about 1% cc.) is shaken with 100 cc. of fuel oilfor 2 minutes. At aperiod up to a week, a settling slowly oc-' curs. Aneffective additive retards the settling and main- Erdco Test.

. cessive pressure.

to develop a differential pressure across the filter of 25 in. Hg isdetermined. It is apparent that the longer the time, the more effectiveis .the additive. However, with a very effective additive, the time toreach a differential pressure acrosslthe filter of 25 in. Hg islengthenedbeyond reasonable limits that the test is stopped after about300 minutes and the differential pressure at that time is reported. v 1i Example I The additive used in this example was prepared by thecondensationof 0.4 equivalent (64.6 g.) ofN-(Lniethylhexadecy1)-ethanolamine and 0.4equivalent (42 g.) of PetrexAcid. As hereinbefore set forth, Petrex Acid is the react-ion product ofterpene and maleic anhydride, and the properties of this acid havebeenset forth hereinbefore. The condensation was efiectedinsubstantially the same manner as hereinbefore described. cc. of xylenewas used as the solvent, and the mixture was boiled under refluxconditions fora period of 13.5 hours at an average temperature of jl55C. The xylene was removed bydistilling under vacuum.

A 2% solution of the condensation product inbenzene was prepared, and1.14 cc. by weight of this solution or about 0.02% by weight ofactiveicomponents'was incorporated in 100 cc. of a No. 2-fuel oil andtested accord-, ing to the Fuel Oil Suspension Test? heretoforedescribed. When evaluated according to this test, the fuel oilcontaining this additive was reported as good. 'In contrast, a controlsample of the fuel oil (sample not containing this additive), whenevaluated in this test, was reported as poor. As 'hereinbefore setforth, the results reported as good mean that the carbon black wasmaintained in suspension and did not settle out. On the other hand, theresults reported as poor mean that the carbon black settled out ofsolution and therefore would plug filters, burnerftips, etc.,during use.

' Example [I Another sample of the condensation product prepared in themanner described in Example I was utilized in the The heated oil used inthis test was a commercial range oi-l. 0.001% by weight of the condensation product described in Example I was incorporated in a sample ofthe oiland run in the Erdco Test. After 300 minutes, the differentialpressure across the filter was. only 3.8 in. Hg. On the other hand, acontrol sample (not containing this additive) reached a differentialpressure across the filter of 25 in. Hg in about 66 minutes.

Here again, it will be noted that the additive was very effective inreducing plugging of the filter and served to considerably prolongoperation without developing ex- Example 111 v The additive used in thisexample was prepared by the condensation of 0.2 equivalent ofN-(l-methylh'exa.

decyl)ethanolamine, 0.00756 equivalent of diethylarnino- 0 ethanol and0.2 equivalent of Petrex Acid. The condensation was effected insubstantially the same manner as described in Example I. The additive isa polyesterpolyarnide condensation product.

A 2% solution of the condensation product inbenzene was prepared, and1.14 cc. by weight of this solution or about 0.02% by weight of activecomponents was in corporated in 100 cc. ofa #2 fuel oil and testedaccording to the Fuel Oil Suspension Test heretofore described. Whenevaluated according to this test, the fuel oil containing this additivewas reported as good. In

contrast, a control sample of the fuel oil (sample not containing thisadditive when evaluated in this test, was reported as poor. Ashereinbefore set forth, the results reported as good mean that thecarbon black was maintained in suspension and did not settle out. On theother hand, the results reported as poor mean that the carbon blacksettled out of solution and therefore would plug filters, burner tips,etc, during use.

Example I V Another sample of the condensation product prepared in themanner described in Example III was utilized in the Erdco Test. Theheated oil used in this test was a commercial range oil. 0.01% by weightof the condensation product described in Example III was. incorporatedin a sample of the oil and run in the Erdco Test. After 300 minutes, thediiferential across the filter was only 0.1 in. Hg. On the other hand, acontrol sample (not containing this additive) reached a differentialpressure across the filter of 25 in. Hg in about 200 minutes. Hereagain, it will be noted that the additive was very effective in reducingplugging of the filter and served to considerably prolong operationwithout developing excessive pressure.

- Example V The additive used in this example was prepared by thecondensation of 0.2 equivalent of N-(1-methyldodecy1)- ethanolamine,'0.00756 equivalent of diethylarninoethanol and 0.2 equivalent of PetrexAcid in substantially the same manner as described in Example I.

When incorporated in #2 fuel oil in a concentration of about 0.02% byweight of active component and tested according to the Fuel OilSuspension Test, the fuel oil containing the additive was reported asgood. Here again, it will be noted that the additive of the presentinvention maintained the carbon black in suspension and therefore willnot plug filters, burner tips, etc., during use.

Example VI Example VII Another sample of the condensation productprepared in the manner described in Example IV was utilized in the ErdcoTest as described in Example II. After 300 minutes, the differentialacross the filter of the sample containing the additive was 0.3 in. Hg.A control sample of the oil (not containing this additive) reached adilferential across the filter of 25 in. Hg in 66 minutes.

Example VIII The additive used in this example was prepared by thecondensation of 0.2 equivalent (55.9 g.) of N-(l-heptadecyloctadecyl)-ethanolamine and 0.2 equivalent (21 g.) of Petrex Acid.Xylene was used as the solvent and the mixture was refluxed for 15.5hours, after which the xylene was removed by vacuum distillation.

When incorporated in #2 fuel oil in a concentration of about 0.2% byweight of active component and tested according to the Fuel OilSuspension Test, the fuel oil containing the additive was reported asgood. As mentioned earlier, this indicates that the additive will notplug filters, burner tips, etc. during use.

Example IX 0.01% of the condensation product prepared according setforth hereinbefore.

Example X The additive used in this example was the condensation productof 0.2 equivalent.(55.9 g.) of N-(l-heptadecyloctadecyD-ethanolaminewith 0.2 equivalent (39 g.) of Lewisol 40 Acid. The properties of thisacid have been 100 g. of xylene was used as the solvent and the mixturewas refluxed for 23 hours,

following which the xylene was removed by vacuum distillation.

When tested according to the Erdco Test, 001% by weight of this additivein the fuel oil served to extend the differential across the filter toonly 0.4 in. Hg after 300 minutes. On the other hand, a control sampleof the fuel oil reached a differential pressure of 25 in. Hg in 82minutes.

Example XI 21.5 g. Petrex Acid (0.2 equivalent) and 71.4 g. of N (1methyloctadecyl) ethanolamine (0.4 equivalent) were refluxed in g. ofxylene. 1.6 cc. of water were collected. The product freed from xylenehas a basic mol combining weight of 818 and an acid number of 4.6.

0.001% by weight of the condensation product was incorporated in rangeoil and gave a difierential pressure of 20 in. Hg after 300 minutes whenevaluated in the Erdco Test.

I claim as my invention:

1. The condensation product of an N-aliphatic hydrocarbon substitutedmonoalkanolamine having from about 6 to about 50 carbon atoms in thealiphatic hydrocarbon substituent with the reaction product, formed at atemperature of from about C. to about 300 C., of a terpene hydrocarbonof the formula C H and a compound selected from the group consisting ofmaleic, fumaric, citraconic, mesaconic, aconitic and itaconic acids andtheir anhydrides and esters, said condensation product having beenformed at a temperature of from about 80 C.

" to about 200 C. and with the use of from about 0.5 to

about 2 equivalents of total acid and potential acid groups in saidreaction product per equivalent of hydroxyl groups in the alkanolamine.

2. The condensation product of claim 1 further characterized in thatsaid monoalkanolamine is an ethanolamine.

3. The condensation product formed by condensing at a temperature offrom about 80 C. to about 200 C. one equivalent of an N-alkylmonoalkanolamine having from about 15 to about 40 carbon atoms in thealkyl group with one equivalent of the reaction product of a terpenehydrocarbon of the formula C H and a compound selected from the groupconsisting of maleic, fumaric, citraconic, mesaconic, aconitic anditaconic acids and their anhydrides and esters, said reaction producthaving been formed at a temperature of from about 150 C. to about 300 C.

4. The condensation product of claim 3 further characterized in thatsaid monoalkanolamine is an ethanolamine.

5. The condensation product formed by condensing at a temperature offrom about 80 C. to about 200 C. one equivalent of an N-aliphatichydrocarbon substituted monoalkanolamine having from about 6 to about 50carbon atoms in the aliphatic hydrocarbon substituent with oneequivalent of the reaction product of a terpene hydrocarbon of theformula C H and maleic anhydride, said reaction product having beenformed at a temperature of from about 150 C. to about 300 C.

6. The condensation product formed by condensing at a temperature of.from about 80C. to about 200 C. one equivalent or" an N-alkylmonoalkanolamine having from about 15 to about 40 carbon atoms in thealkyl group with one equivalent of the reaction product of a terpenchydrocarbon of the formula C H and maleic anhydride, said reactionproduct having been formed at a temperature of from about 150 C. toabout 300 C.

7. The condensation product of claim 6 further characterized in thatsaid monoalkanolamine is N-(l-methylhexadecy-l) -ethanolamine.

8. The condensation product of claim 6 further characte'rized in thatsaid monoalkanolamine is N-(l-methyldodecyD-ethanolamine.

9. The condensation product of claim 6 further characterized in thatsaid rnonoalkanolamine is N-(l-heptadecyloctadecyl) -ethanolamine.

10. The condensation product of claim 6 further characterized in thatsaid monoalkanolamine is N-(l-methyloctadecyl) -ethanolamine.

References Cited in the file of this patent UNITED STATES PATENTS2,300,566 Hahn et a1 Nov. 3, 1942 2,344,831 Ott Mar. 21, 1944 2,456,177Cupery Dec. 14, 1948 2,607,762 Bowen Aug. 19, 1952 2,681,894 Hoenel June22, 1954 2,723,195 Blake Nov. 8, 1955 OTHER REFERENCES Rowland: Maleicand Fumaric Resins, pages 83-93,

20 Interchemical Review, vol. 5, No. 4 (Winter 1946-1947).

1. THE CONDENSATION PRODUCT OF AN N-ALIPHATIC HYDROCARBON SUBSTITUTEDMONOALKANOLAMINE HAVING FROM ABOUT 6 TO ABOUT 50 CARBON ATOMS IN THEALIPHATIC HYDROCARBON SUBSTITUENT WITH THE REACTION PRODUCT, FORMED AT ATEMPERATURE OF FROM ABOUT 150*C, TO ABOUT 300*C, OF A TERPENEHYDROCARBON OF THE FORMULA C10H16 AND A COMPOUND SELECTED FROM THE GROUPCONSISTING OF MALEIC, FUMARIC, CITRACONIC, MESACONIC, ACONIC ANDITACONIC ACIDS AND THEIR ANHYDRIDES AND ESTERS, SAID CONDENSATIONPRODUCT HAVING BEEN FORMED AT A TEMPERATURE OF FROM ABOUT 80*C, TO ABOUT200*C AND WITH THE USE OF FROM ABOUT 0.5 TO ABOUT 2 EQUIVALENT OF TOTALACID AND POTENTIAL ACID GROUPS IN SAID REACTION PRODUCT PER EQUIVALENTOF HYDROXYL GROUPS IN THE ALKANOLAMINE.